title: Metal-free halonium mediated acetate shifts of ynamides to access α-halo acrylamides/acrylimides.
abstract: A metal-free acetate shift of 3-acetoxy ynamides to access α-iodo, bromo, and chloro acrylamides/acrylimides under very mild conditions is demonstrated. The inherent alkyne activation of ynamides is sufficient to ensure the α-halo acrylamides/acrylimides in high yields without the addition of a catalyst. In all cases high Z-stereoselectivity is observed.
authors.affiliation: Department of Chemistry, Center for Insoluble Protein Structures (InSpin), Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.
authors.forename: Søren
authors.initials: S
authors.lastname: Kramer
authors.forename: Stig D
authors.initials: SD
authors.lastname: Friis
authors.forename: Zhuo
authors.initials: Z
authors.lastname: Xin
authors.forename: Yann
authors.initials: Y
authors.lastname: Odabachian
authors.forename: Troels
authors.initials: T
authors.lastname: Skrydstrup
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000178:Acrylamides / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D007094:Imides / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000085:Acetates; D000178:Acrylamides; D000577:Amides; D006219:Halogens; D007094:Imides